Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Tribenuron-methyl

HRID 649434Notes

Reaction equation

HRID 649434 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12])([O:3][CH3:4])=[O:2].[CH3:17][O:18][C:19]1[N:24]=[C:23]([CH3:25])[N:22]=[C:21]([NH:26][CH3:27])[N:20]=1>ClCCl>[CH3:17][O:18][C:19]1[N:24]=[C:23]([CH3:25])[N:22]=[C:21]([N:26]([CH3:27])[C:15]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:1]([O:3][CH3:4])=[O:2])(=[O:12])=[O:13])=[O:16])[N:20]=1

Participants

4

Reactant 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 1607791,3,5-Triazin-2-amine, 4-methoxy-N,6-dimethyl-

Product 1

HCID 153909Tribenuron-methylYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-carbomethoxybenzenesulfonyl isocyanate (22.4 g 93.0 mmol) in dichloromethane (100 mL) was added 2-methoxy-4-methyl-6-methylamino-1,3,5-triazine (10.7 g, 69.6 mmol), followed by a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane. After stirring overnight at ambient temperature under a nitrogen atmosphere, the reaction mixture was concentrated in vacuo. The residue was triturated with diethyl ether and then washed with 1-chlorobutane to yield the title compound as a white powder (27.8 g, m.p. 126°-131° C.).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was triturated with diethyl ether
  3. washwashed with 1-chlorobutane

Sources & evidence

ORD record
ord-e519d64bcb4542259b887031c87d5d22
Source dataset
uspto-grants-1988_04
Patent number
US04740234

Reaction notes

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